Stereoselective synthesis of trans-dihydronarciclasine derivatives containing a 1,4-benzodioxane moiety
Gábor Varró1,2, Balázs Pogrányi1, Alajos Grün1
11Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budafoki út 8, Budapest, 1111 Hungary.
Abstract:
Some new trans-dihydronarciclasine derivatives containing a 1,4-benzodioxane moiety were stereoselectively synthesised using our feasible and efficient method developed recently. These new phenanthridone alkaloid analogues were obtained in both racemic and optically active forms. High enantioselectivities (up to 99% ee) were achieved by applying (8S,9S)-9-amino(9-deoxy)epiquinine as an organocatalyst. Due to a side reaction, various methoxyphenanthridine regioisomers were also prepared which afforded further synthetic trans-dihydronarciclasine analogues modified in the ring A of the phenanthridone scaffold.
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